82772-34-7Relevant academic research and scientific papers
Preparation of functionalized aryl magnesium reagents by the addition of magnesium aryl thiolates and amides to arynes
Lin, Wenwei,Sapountzis, Ioannis,Knochel, Paul
, p. 4258 - 4261 (2007/10/03)
(Chemical Equation Presented) Reactive arynes, which are readily generated by the reaction of ortho-iocloarylsulfonates with iPrMgCl, undergo the smooth addition of various magnesium nucleophiles like magnesium thiolates, selenides, and amides. In all cases the resulting functionalized aryl magnesium species can be trapped by an electrophile leading to highly functionalized aromatic compounds (see scheme).
Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates
Calestani, Gianluca,Leardini, Rino,McNab, Hamish,Nanni, Daniele,Zanardi, Giuseppe
, p. 1813 - 1824 (2007/10/03)
Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.
Meta Functionalization of Anilines and Phenol
Fukui, Mineo,Ikeda, Toshiya,Oishi, Takeshi
, p. 466 - 475 (2007/10/02)
Base-promoted proton abstraction from ?-(N-tert-butyldimethylsilyl-N-methylaniline)chromium tricarbonyl (3) took place predominantly at the meta position and variously meta-substituted N-methylacetanilides 4 were obtained after reactions with electrophiles followed by oxidative decomplexation and N-acetylation.Application of the present method to variously N,N-disubstituted anilines 5 and phenols 7 was then examined and the corresponding meta substituted anilines 6 and phenol 9 were obtained.Keywords - metalation of aromatic ring; chromium tricarbonyl complex; tert-butyl dimethylsilyl protecting group; meta-substituted anilines; meta-substituted phenol; electrophilic substitution
META FUNCTIONALIZATION OF ANILINES AND PHENOL
Fukui, Mineo,Ikeda, Toshiya,Oishi, Takeshi
, p. 1605 - 1608 (2007/10/02)
Regioselective introduction of various functional groups on the meta-position of anilines and phenol was achieved by proton abstraction from chromium tricarbonyl complexes 3,5,7 with n-BuLi, followed by the addition of electrophiles and decomplexation.
